LEADERS ASK THE RIGHT KINDS OF QUESTIONS

When you were a young leader, did you ever ponder the kinds of questions you were asking your direct reports?

Did you plan the questions in advance?

Did you shape the questions to gain specific results you were seeking from the conversation?

Did you pose your questions in a manner that would not only help you as a leader gain insights, but would correspondingly help your teammate grow?

I know that when I was a young leader, I never thought about the questions I posed in advance, whether I was in a one-on-one weekly meeting or in a weekly all-staff meeting. I knew what I wanted to get at, what I wanted to learn, what we as a group needed to get to, and I asked the first questions that popped into my head.

I may have been helping myself obtain answers, but I was not helping my teammates grow. I was not helping them gain self-confidence. I was not at all nurturing their own leadership potential. I was merely thinking about me as the leader and what I wanted to know that would move us forward toward my desired goal.

This, I am not proud to admit, was a form of ego-focused leadership, of leadership aimed at getting to the right answer as soon as possible, and of leadership focused on my own goals at the expense of my team member’s professional goals. In his context, I was paying no attention to their personal growth journeys or their needs to learn and understand.

I was reminded of the power of great questions again this week when I read the latest monthly blog post from renowned leadership coach Scott Eblin. Scott was a longtime faculty member at the Georgetown University Leadership Coaching Program, the program where I gained my leadership coaching training before becoming a certified leadership coach. Scott has coached and consulted across the country for Fortune 100 companies, leading non-profits and significant government agencies. His blog is well worth subscribing to and offers meaningful wisdom each month. I encourage you to sign up for it.

This month Scott writes about that critical skill of good leaders, asking important and well-thought-out questions that engage our teammates and motivate them to think. Don’t forget – our teammates grow most when they are thinking. And when they are thinking in silence, we know they are truly pondering our inquiry. Please do not rush to fill in that silence. Let it percolate – you will receive a well-organized response.

Here are the big what questions Scott suggests leaders utilize to motivate their teammates and to strive for alignment within their team or department. How many of these questions do you have in your leadership arsenal?

1. What are your biggest strategic priorities in this situation?
→ Surfaces overarching objectives that may be driving their stance.

2. What risks or unintended consequences do you see if we move forward with this approach?
→ Uncovers hidden concerns that could derail execution later.

3. What would success look like not just for you, but for the business as a whole?
→ Expands the conversation beyond personal or functional priorities to enterprise impact.

4. What underlying factors or constraints are shaping your perspective on this issue?
→ Reveals external pressures (e.g., regulatory, competitive, investor-driven).

5. What past experiences—good or bad—are informing your thinking on this decision?
→ Helps understand whether prior failures or successes are influencing current risk tolerance.

6. What are the biggest misalignment risks you see between leadership, employees, customers, the board, and other key stakeholders?
→ Identifies potential friction points that could slow or block progress.

7. What does this decision look like from a competitor’s perspective?
→ Encourages a thinking shift from inside-out to outside-in.

8. What would need to be true for you to feel fully confident in this decision?
→ Surfaces conditions for buy-in and signals potential areas of compromise.

9. What blind spots might we have in our current thinking?
→ Encourages executives to challenge assumptions and stress-test decisions.

10. What’s the best way to ensure alignment and execution at scale?
→ Moves the conversation beyond decision-making into implementation and accountability.

Please consider and use these powerful questions Scott suggests. Develop your own meaningful what questions.
And create regular significant “what questions” you can ask yourself on a regular basis!

You will become a more effective leader as a result!

If you believe this content would resonate with a friend or colleague, please feel free to forward it along!

-Larry